3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)- → HCID 60004308, compound

Participants

Reaction Conditions

Reaction Steps

(R)-tert-butyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate (1.53 g, 6.67 mmol) was purged with nitrogen, and then was diluted with tetrahydrofuran (20 mL) and cooled to 0° C. in a ice-water bath. Ethylmagnesium bromide (3.34 mL, 10.01 mmol) was added slowly over 10 minutes. The reaction was stirred for 1 h in the ice water bath. After stirring 1 h, the reaction was slowly quenched with 30 mL sat. ammonium chloride. This was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed 1× brine, then dried over sodium sulfate, filtered and concentrated to afford crude (4R)-tert-butyl 4-(1-hydroxypropyl)-2,2-dimethyloxazolidine-3-carboxylate as a colorless oil (1.65 g) which was carried on directly in the next step.

Provenance & Evidence